Method of preparing halogenated nitroalcohols

Abstract

A method of preparing bromonitroalcohols of the formula ##STR1## where R 1 is H, lower alkyl or R 2 , R 2 is R 3 CHOH in which R 3 is H, alkyl or aryl, and X is a halogen, which comprises reacting a halonitroalkane with a substantially nonaqueous solutioln of an aldehyde of the formula R 3 CHO where R 3 is as noted above, in the presence of an alkaline catalyst. R 3 preferably is lower alkyl or monocyclic aryl such as phenyl.

What is claimed is: 
     
       1. A method of preparing a halonitroalcohol of the formula ##STR3## where R 1  is H, lower alkyl or R 2 , R 2  is R 3  CHOH in which R 3  is H, lower alkyl or phenyl, and X is chloro or bromo, which comprises reacting at a temperature between about 20° C. and 60° C. a halonitroalkane with a substantially nonaqueous solution of an aldehyde of the formula R 3  CHO where R 3  is as noted above, in the presence of an alkaline catalyst and recovering the resultant halonitroalcohol. 
     
     
       2. The method of claim 1 wherein R 1  is hydrogen or lower alkyl. 
     
     
       3. The method of claim 1 wherein R 1  is R 2 . 
     
     
       4. The method of claim 3 wherein the aldehyde is formaldehyde. 
     
     
       5. The method of claim 4 wherein the alkaline catalyst is selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, triethyl amine, and n-butyl amine. 
     
     
       6. The method of claim 5 wherein the solvent for the formaldehyde is substantially methanol. 
     
     
       7. The method of claim 6 wherein the halonitroalkane is halonitromethane and the halonitroalcohol is halonitropropanediol. 
     
     
       8. The method of claim 7 wherein the halogen is chlorine or bromine. 
     
     
       9. The method of claim 8 wherein the halonitroalkane is bromonitromethane and the halonitroalcohol is 2-bromo-2-nitro-1,3-propanediol. 
     
     
       10. The method of claim 9 wherein the halonitroalkane is chloronitromethane and the halonitroalcohol is 2-chloro-2-nitro-1,3-propanediol. 
     
     
       11. The method of claim 1 wherein the halonitroalcohol is prepared in a semi-continuous process. 
     
     
       12. The method of claim 1 wherein the halonitroalcohol is prepared in a batch process.